Sex Ed #5: Beginner’s Guide to Anal Sex

I figured you all would like this kind of post, since most of the search terms that bring people to my site have to do with butt sex (and my most-viewed post is about my first time doing it). This guide is mainly written for the receptive partner (the one whose butt will be fucked), but insertive partners (the one fucking the butt) should read it too.
If you’re curious about my first anal sex experience, you can read about it here.

1. Think about whether you actually want to do it.
Do you actually want to have anal sex? If the answer is no, I suggest reading the rest of this guide first, as it may ease any fears you may have. If you still don’t want to do it, then don’t! Don’t let someone pressure you into doing it if you don’t want to; the point of sex is for everyone involved to have a good time, not just one person. Also, apprehension will cause you to be tense during sex, which will likely cause it to hurt.

If you’re curious about the idea but still not sure, you can try some other anal play, which may help you decide whether or not to have full-on anal sex. Read on for more tips on that.

PS: It doesn’t matter what kind of genitals you have, anal sex can feel really good for all different bodies! It’s not pleasurable for all people, but for many, stimulating the anal nerves feels great. Anal sex can also indirectly stimulate the G-spot, and also can stimulate the prostate.

2. Make sure you’re with a partner you trust.
Just as with vaginal sex, anal sex can cause pain and discomfort. You want to make sure your partner will respond appropriately to any concerns you raise before and during the act. Your partner should slow down, pull out a bit, or stop completely if you are in pain.

3. Talk about safe sex with your partner.
Anal sex is the riskiest sexual activity, due to risk of anal tears. These tears not only hurt like a mofo, but also provide an easy path for bacteria and other evil STI-causing organisms/viruses to get into your bloodstream. So make sure you and your partner get tested for STIs, and even if you’re totally STI-free, use a condom anyway, because it’ll help keep things cleaner, and if a penis is involved, it’ll prevent bacteria from going into the insertive partner’s urethra. You may also want to talk about safe-sex tools for manual and oral stimulation of the anus (gloves and dental dams).

4. Wash up.
Sticking stuff up your butt isn’t like sticking stuff into a pile of shit. Your poop is usually stored in the colon, until it’s time for a bowel movement. The penis or dildo will not be going into the colon; it will go into the rectum, which may have some poop in it if you need to use the bathroom. To prevent messes, go to the bathroom and clean around the anus before playtime. (I usually do this right before foreplay.) Enemas generally aren’t necessary, but if it’d make you more comfortable, you can read about them here.

5. Warm up, and USE PLENTY OF LUBE!
Even if you’ve had anal sex many times before, do not go straight into putting the penis/dildo in your ass! It will likely hurt and you may injury yourself. You need to get aroused (to relax your sphincter muscles in your butt) and prepare your ass to have a large object thrusting inside of it.

First, do what turns you on. Touch each other’s genitals, watch porn, dirty talk, lick each other, whatever makes you aroused. Then, start anal play slowly. If you’re into rimming (orally stimulating the sensitive nerves around the anus), you can do that. Many people start out by inserting a finger into the anus, kind of like fingering a vagina (but more slowly!). MAKE SURE TO USE LOTS OF LUBE! The anus and rectum do not self-lubricate, and are sensitive, so if you do not use enough lube, it is more likely to hurt, and you may tear the anal lining. This will hurt even more, and you might even need to get surgery to fix it. Don’t be afraid to ask for more lube at any time during foreplay or sex. Use a water-based or silicone-based lube; many people (like me) prefer silicone, since it lasts longer and is more slippery, but some people are fine with water-based lube.

After inserting one finger and getting comfortable with that, you can insert more. By the way, you can stick your fingers in your own butt, or your partner can stick their fingers into your butt. It doesn’t matter – it’s just a matter of personal preference.

Sex toys are a great way to warm up. Butt plugs, anal beads, and dildos can all help prepare your butt for anal sex. Just make sure any toys you use have a flared base or another design that keeps them from being sucked into your ass. You can read about that here. Don’t forget lube with these as well! But if you’re using a silicone toy, don’t use silicone lube (it may degrade your toys), unless you’ve spot-tested the lube on the toy already and had no problems.

6. Relax, LUBE UP, and stick in the penis/dildo.
Relaxing is super important to prevent pain, discomfort, and injury. So make sure you are relaxed before the penis or dildo goes in.

When it comes to positions, I usually go with doggie style, but lay my head, forearms, and/or upper chest on the bed (or ground, depending on where we’re fucking), and spread my legs a bit. This way, my anus is naturally opened up a bit, which makes things easier, and makes me more relaxed. It’s also good because I’m kind of lazy and don’t like propping myself up. To read up on more anal sex positions, check this out.

Before you stick in the penis or dildo, put on a condom and PUT LOTS OF LUBE ON IT! Then, slowly insert the tip of the penis or dildo. Do this very slowly, take pauses, and make sure the receptive partner is breathing and relaxing. It may hurt at first. If so, pull out and add more lube. Then you can try again. If it keeps hurting, stop and try again some other time.

After a bit more than the tip is in (maybe about 3 inches), try (slowly) thrusting. The insertive partner can control this, or the receptive partner can, depending on positioning and what you’re comfortable with. As you proceed and everything feels fine and dandy, you can increase the speed and depth of penetration. If it hurts, slow down, pull back a bit, and/or add more lube. Soon you will be fucking away!

Make sure to communicate with your partner about how you are feeling during sex! If it hurts, let them know so they can adjust. If it feels awesome, let them know too!

7. Clean up, and talk with your partner.
Following the afterglow of sex (and in my friend’s* case, listening to “I Just Had Sex” by the Lonely Island after every sexual encounter), it’s time to clean up! Remove the condom, clean off your genitals and ass, and wash your hands and any toys you used. It’s also a good idea to talk with your partner about how you felt during sex, what worked, and what didn’t, so next time will be even better!

Other important stuff:
-Do not stick the penis/dildo into a vagina after it’s been in an ass without cleaning the penis/dildo or changing condoms first! This will introduce bacteria that should not be in a vagina, and may cause infection. (It’s fine to go from vagina to ass, just not ass to vagina.)

-Do not use any sort of desensitizing wipe or cream! Pain is your body’s way of telling you something is wrong. If you take this away, injury is very likely.

-It’s not gay for a dude to stick something in his ass! Many straight dudes think that if a woman licks his anus or sticks her fingers/a toy in his ass, that makes him gay. That’s totally not true. Sexual orientation isn’t about the acts themselves, but about the person you’re doing them with. (For example, if a lesbian enjoys being penetrated with a strap on by her female partner, does that make her straight?) If you were born with a penis, then you have a prostate, and sticking stuff in your ass can stimulate the prostate (which feels really good!).

Thanks for reading, and have fun fucking! Do you like butt sex? What was your first time like? Did I forget any important tips? Any questions? Let me know in the comments below!

*By my friend, I mean me. But I stole the idea from my friend.

REVIEW: Chemistry, Vol. 1

(I realize my first review is supposed to be of the Tantus Ryder, but I can’t find my camera charger to take pictures of it! So I’m doing a porn review instead.) 

Chemistry, Vol. 1 is like a reality show, except it’s about 500 times better, since there are naked people and none of them are annoying or catty. The premise is that Tristan Taormino found 7 porn stars and put them in a house (with cameras) for 36 hours. The stars get to decide who they have sex with, what they do in these scenes, and when and where to do these scenes.

Okay, that last part is mostly true. In the behind-the-scenes footage, you see (an extended scene of) Tristan talking with all the performers before they go smush their genitals together. She mentions that they each know, from emails Tristan has sent, who they’re going to have sex with at least once, but where and when aren’t planned. They also have a “sign-up sheet” for sex. This is because there are a limited number of cameras, so if all of them have sex at the same time, someone’s sexy time won’t get filmed.

The movie focuses a lot on the connections and chemistry between the performers (hence the title). In between all the fucking, the performers talk about their experiences in the house, how they feel about the other stars, what they’re turned on by, etc. They also have philosophical rants about the porn industry, and talk about their lives in and out of the industry.

Since spontaneity is part of the premise, I’m not going to give a scene-by-scene rundown, but I’ll talk a little bit about each performer and the sex in general.

Mr. Marcus: He was the only name I recognized before watching this movie. He’s very charming and considerate of his co-stars, and in my opinion, the best looking out of the 3 male stars.

Jack Lawrence: He loves licking pussy. A lot. He talks about it a lot, and he does a lot of it in this movie. He’s not into rough sex (although he’ll compromise a bit to make a girl happy) – he’d rather just cuddle and lick pussy. And suck on his partners’ toes during sex.

Kurt Lockwood: A lot of the other stars expressed concerns about working with him, since apparently he had been difficult to work with in the past, but after the fact, everyone agreed that he is a funny and caring guy who has changed since he first got into the industry.

Marie Luv: Out of all the performers, she seems to have the most chemistry with her partners. Although I think the behavior of all the performers is mostly genuine, I feel like hers is the most authentic.

Taryn Thomas: She’s hot, but in her scene with Kurt, she acts very much like a typical porn star (loud, high-pitched noises and dirty talk). She reminds me a lot of Sasha Grey in this regard. If you want to skip out on her talking about how much of a whore she is, I’d suggest skipping this scene.

Mika Tan: She is super fun, bubbly, and outgoing, and loves all sorts of sexy activities. She’s also very attractive and likes going down on other women.

Dana DeArmond: She seems like a very genuine person. She reveals her insecurities in the “confessionals”, and even says, regarding her scene with Mika and Jack, that it wasn’t great. I consider that refreshing, because she’s actually being honest.

For a porn movie, the sex is very realistic. They actually show the performers using lube – the bottle, squeezing it out, everything! The performers aren’t afraid to make weird noises/faces that real people make during sex. They have real connections with each other and speak up if something is bothering them (for example, while having sex with Mr. Marcus, Dana expresses pain twice, and he adjusts accordingly). The performers themselves are also fairly realistic-looking. Sure, they’re all attractive, but they have not been heavily made up (or shot with bright lighting to hide blemishes), even though the film is in HD. You can see pimples on a few of the performers’ asses during close-ups.

Speaking of close-ups, there are a lot of them. There is also a lot of oral sex. If you don’t like either of those things, you probably won’t like this movie.

There’s also a LOT of sex toys! I saw Pure Plugs (prototypes, since they were in development at the time of filming), a Fun Wand, a LAYAspot, and a Hitachi Magic Wand. There were other toys too, but I couldn’t identify them (or my shitty DVD player skipped over them). They use strap-ons, vibrators, butt plugs, glass dildos, and anal beads – these toys are used on both men and women, which is refreshing to see! There are two (very hot) scenes that involve pegging, which is rare to see in a porn movie targeted to heterosexuals. Some of the girls use vibrators on their clits during sex, validating female pleasure.

There were only a few things I didn’t care for. I didn’t particularly like the scene between Mika, Jack, and Dana; Jack seemed to feel very out of place. I think the sex was too rough for his liking, with Mika taking on a dominant role, and Dana being the submissive. Jack later acknowledges he was feeling out of it, but blames it on him being hungry.

Also, if the performers used condoms (which Tristan has not required until recently), I would get to call this “the best example of realistic and safe sex I’ve ever seen in porn.” (The current holder of that title is the free educational porn series Tristan made for Smitten Kitten’s website.) If Tristan makes another volume of Chemistry (there are 4 volumes so far), I’ll probably get to make this statement!

I would have also appreciated some more queerness. There is girl-girl action, but aside from some flirtation and fondling, all of it is in the presence of a man. There is also no action between men. This is something I would’ve liked to see, and I bet many other queers would’ve liked to see it too, but I understand that Tristan was trying to target the large heterosexual market.

The feature film is almost 3 hours long, and there is over one hour of bonus footage, including more sex scenes! There is also a feature called the Positions Room. It includes 5 montages of clips from the movie: “pussy eating”, blow job, missionary, doggie, and cum shot. This is fantastic if you know exactly what kind of sex you want to get off to. Overall, Chemistry, Vol. 1 rocks. It’s super hot, interesting, realistic, sex positive, and female-friendly. I definitely recommend it! You can buy it from Tristan’s website here.

Thank you so much for reading my first review! Have you seen any of the movies in the Chemistry series? What do you think of them? Let me know in the comments below! Also, since this is my first review, I’d love to hear what you think about the review itself. If you have any comments, suggestions, or constructive criticism, please let me know!

Note: No one is paying me to review this. I got the DVD as a “thanks for calling” gift when I called in to Sex Out Loud Radio.

Where the hell is Rosaline? + sex update

If you don’t want to read about things like emotions and mental health, and just want to read about my sex life (which I totally understand!), scroll to the bottom of this post to get what you’re looking for.

So this is in two parts, because I’m too lazy to revise the first part (which I wrote a month ago) to make it applicable to now.

November 2:

So you may have noticed that I haven’t posted for over a month. And maybe you’ve wondered why.

Well, the reason is because my depression has gotten worse.

A combination of loneliness, the feeling of rejection, lack of motivation to do anything, and the fact that my anti-depressant dosage (which I started this summer) is so low that it’s apparently not even supposed to be effective. (Then why the hell did my doctor give it to me?)

Oh, and it’s been harder to have orgasms (possibly because of my anti-depressant). Which is totally fine when I’m masturbating, because I enjoy taking longer when I masturbate (it usually is over pretty quickly). But when I’m with my boyfriend, it takes him longer, and it’s hard to have an orgasm. Also, since I only get to see my boyfriend about once a month, the long break between each visit makes my vagina go back to “pretty much a virgin” mode (I usually only stimulate my clit during masturbation, so my vagina doesn’t get any action when he’s gone). Sex has been hurting, not just because it stretches my tight vag open a lot, but also the walls of my vagina get irritated. Even the Pure Wand is kind of uncomfortable!

My boyfriend and I also had some problems lately. Like relationship problems. I don’t want to talk about it that much since we are now fine and dandy but the wounds are still fresh (and he’ll be proofreading this post for me). That conflict really took a toll on my mental health.

Lack of motivation has probably been the biggest reason why I haven’t blogged, though. I’m not saying that blogging is boring to me, and now that I’m typing again, I’m feeling a lot better about it. It’s just that I’ve lost motivation to do a lot of things. If I weren’t so academically oriented, I’d probably be failing my classes. My room is a fucking mess because I am extremely unmotivated to clean. Or do a billion different other things. Sometimes I’m even unmotivated to masturbate, even if I’m horny. Sometimes I’m too lazy to plug in my defective Salsa (which I’m too unmotivated to send in for repair). I haven’t had the desire to use a lot of my sex toys, except for the Salsa. (By the way, I am naturally a very motivated person, and definitely the opposite of lazy, so this is certainly a symptom of depression and not a character flaw.)

And writing reviews? I bet you can guess… unmotivated to do them.

I wish I could write a review this weekend, but since my boyfriend is here (and providing motivation), I really need to get other things done this weekend. Like clean. And take a shower. And do laundry. And go to CVS. And buy Drain-O (I can’t find the hair catcher thing that goes over my tub drain, so now it’s clogged). And of course, homework too.

And I should probably have sex with my boyfriend too. We tried last night but it kept hurting.

So I would write more about the feeling of rejection, but I don’t really feel like it. I should probably do other things right now, anyway.

Like call my doctor about my meds.

Thank you all for reading, and understanding. Well, hopefully you understand. If you don’t… oh well.

December 2:

So I was going to post that stuff above that day, after my boyfriend proofread it. However, he never actually did. When I typed that post up, he was sleeping, and when he got up, we started touching each others’ naked bodies, and then we had a bunch of other stuff to do.

So since then, let’s see… what has changed? I’m still unmotivated to send in my Salsa. I’m still depressed, and feeling lonely, rejected, sad, etc. But I also have felt more regret recently. I feel like I’ve screwed up certain parts of my life, and I just want to relive the past 3 months, so I could do things right this time. But I can’t, which really, really sucks. I’ve been having suicidal thoughts lately, too. Don’t worry, though. I know the hotline numbers and everything.

I’m on new meds though! But I need a higher dose. My shrink put me on a really low dose to get me used to it, I guess. At least my sexual problems are almost completely gone! (Sex still hurts a bit sometimes, but definitely less than before. And I can have orgasms again! Yay!)

I really shouldn’t be up right now. I have a 9am class and I need sleep. But fuck that shit. Who needs sleep? (I actually do. But I guess I’ll deal.) I just really wanted to type this right now, since I started thinking about it in the shower for some reason.

Okay, time for the sex update:

My boyfriend and I managed to have anal sex to completion last month! And unlike last time (where it felt more interesting than pleasurable), it felt really, really good. Well, at least it did the second time he stuck his penis in. The first time, I was not warmed up enough, and it hurt quite a bit. So we then used the Tantus Ryder to warm me up some more, while he used the Salsa on my clit. Then when he entered me again (using lots of Spunk Lube Silicone to keep things slick), it went in nicely and felt AMAZING.

I just saw my boyfriend last week and we were naked for a lot of that time, but nothing too interesting to note. But my mouth has been getting sore lately while giving oral sex. It didn’t used to. Weird. It happened while we were 69ing, but I just used my hand to finish him off (the tip of his dick was still in my mouth, but it wasn’t moving).

So that’s all for now. I didn’t get on Twitter or check my email tonight, because I really have to go to bed, but hopefully I’ll get around to that within a few days, and hopefully I’ll get back to posting more soon. Hope you all are doing well!

My first time: Anal sex

NOTE: This is not my attempt at writing erotica. I use too many anatomical words for it to be erotic. I just wanted to share my experience, for knowledge’s sake. UPDATE: To see my guide to anal sex, click here.

About 6 months ago, I remember saying the words “I’ll never have anal sex.” Fast forward to two months ago: My boyfriend and I are on his floor – I’m on top of him, leaning back, and his dick is in my ass.

So how did that happen? One thing that many people are worried about with anal sex is making a mess and getting fecal matter on the penis/dildo/whatever’s going into the butt. I was worried about this too, and that’s why I didn’t want to try anal. But through research and education (thanks, Internet!), I learned that this is usually not the case. Poop is usually stored in the colon, and only stored in the rectum (which comes right after the anus) temporarily, when a person needs to use the bathroom. So I learned an important lesson: Just poop and clean around the anus beforehand. You’ll probably be fine.

My boyfriend and I actually started talking about anal play (or rather just “teasing”) about two or three months before our anal sex encounter occurred. He said he wasn’t comfortable with the idea, but he’d probably warm up to it. He eventually started lightly stroking the area around my anus (such a tease!), which made me want a lot more. On the day we ended up having anal sex, we weren’t actually planning on it beforehand. We were passionately making out in his bed, and he was stroking me around the opening, so I said “I just went to the bathroom, so you can tease me a bit more, if you’d like.” So he stuck his finger in. And it felt good! It felt weird as he pulled it out though; it felt like I was pooping. This is why I’m very glad I had already used the bathroom, so I didn’t poop on his finger. I asked to see his finger, and it wasn’t messy at all! There was just a clearish film present, and that wasn’t bad at all. He asked if I wanted two fingers inside. I said yes, and after he penetrated me that way for a while, I asked if he could use the tip of his penis. “You really want me to?” he asked. “Yes I do,” I said. “We can stop if it hurts.” He put on a condom (WHICH WAS SUPER IMPORTANT so germs from the anus didn’t enter his body through the urethra) – and he probably should have put some more lube on the already-lubricated condom, but I’d forgotten my lube at my house, and we were planning on going slowly anyways.**** And then he slowly entered me… and it felt good! Not amazing, not nearly as good as vaginal sex, but it was interesting. I asked him to go in further, so he did.

Then he started thrusting, and the bed was shaking and rattling too much (and his family was downstairs), so we got on the floor instead. Unfortunately, we couldn’t find a position that was both quiet and stimulating, and his penis kept slipping out, but the experience was pleasurable for both of us (except for when he went too deep – he said that was too tight for him). The thrusting did not feel like I was about to poop, as his fingers had done earlier, so I was very happy about that. He didn’t end up ejaculating because of our problems with positioning, but it was a good experience, and we hope to try it again sometime soon.

I hope my story was enlightening and maybe answered some questions you had about anal sex! Have you done it before? What was your experience? Anything else you’d like to say? Let me know in the comments below!

****Please use lots of lube! During this encounter, he was not fully erect, so we didn’t need as much lube. If you don’t use enough lube, it will likely hurt, and you could tear the lining of the anus or rectum! This will provide a direct path for bacteria to get into your bloodstream, which would totally suck because infections are no fun!